The Pathless Path with Paul Millerd
The Pathless Path is hosted by Paul Millerd - a writer, creator, and consultant. He has conversations with freelancers, self-employed entrepreneurs, creators, and vagabonds who share their perspectives on their relationship with work, burnout, bootstrapping, indie hacking, remote work, reinvention, creativity, sabbaticals, leisure, self-employment, unconventional living, and digital nomadism. Past guests include Ali Abdaal, Russ Roberts, Kevin Kelly, Khe Hy, David Senra, Derek Sivers, Joe Hudson, Luke Burgis, Ben Hunt, Dan Vassallo, Steph Smith, Alex Pang, Visakan Veerasamy, Michael Ashcroft, Kyla Scalon, Trung Phan, Justin Welch, and more.
Latest episodes
Apr 3, 2023 • 34min
#140 Tom Peters - Fired from McKinsey to Top Business Thought Leader
I'm sharing this conversation I had a couple of months ago with Tom Peters. Our convo got cut a bit short but it was a fun conversation reflecting on his trajectory, why he got kicked out of McKinseyTo learn more about Tom: His Website
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here
Mar 27, 2023 • 52min
#139 Compounding Memes - Trung Phan on his great grandfather, living abroad, the expat community in Asia, writing, working at The Hustle, children and work, balancing his various activities, going solo, and playing the long game
Trung is a writer at Workweek, cofounder of bearly.ai, and co-host of the Not Investment Advice podcast. He is passionate about playing the long game and unleashing the power of compounding.🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @TrungTPhanWebsite: trungtphan.comBearly.AIPodcast: Not Investment AdviceTrung's writing at Bloomberg and Workweek Trung's Newsletter⌛TIMESTAMPS(02:12) - College and getting up late
(04:44) - Trung's great grandfather - Vietnamese hero
(09:31) - Vietnam, important lessons from living abroad
(22:05) - Writing & productivity
(42:49) - Kids, work & flexibility
(46:43) - Playing the long game
📕Buy Paul’s Book (Published Jan 2022): The Pathless Path😁👉😁 Want To Connect, Create & Root For Others On The Pathless Path? - Join 100+ Others In The Find The Others Community📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here
6 snips
Mar 20, 2023 • 1h 12min
#138 Money & The Creator Economy - Steph Smith on our lack of wisdom about money, reaching "ice cream freedom", The Hustle, balancing employment and side gigs, unconventional paths, opportunities in the creator economy and how not to get disappointed at your wedding
Steph Smith is the host of the a16z podcast and is an online creator, former consultant, former digital nomad and all-around badass. We talk about money, work, relationships, and weddings...🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @stephsmithioSteph's book: doingcontentright.coma16z PodcastThe Sh*t You Don't Learn in School PodcastBlog: stephsmith.io⌛TIMESTAMPS(01:19) - The scripts that Steph grew up with
(03:47) - Perceptions of money over time
(29:15) - Working at The Hustle
(33:57) - A16Z and Beginner's Mindset
(38:04) - Solving the life puzzle with a partner
(46:56) - Scripts around kids
(52:20) - Avoiding long wedding planning cycles
(56:10) - Full-time employment and podcasting
(58:01) - Opportunities in the creator economy
(01:02:23) - Is Paul underpricing his book?
(01:05:57) - The most interesting opportunities in the creator economy
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here
11 snips
Mar 13, 2023 • 1h 10min
#137 Life as Conversation - Russ Roberts on his relationship with his father, starting the EconTalk podcast in 2006, Adam Smith, why people want to be "lovely", aiming high, why it's hard to have fun, misunderstandings of the academic world, and moving to Israel in his 60's
Russ is an economist, a research fellow at Stanford University's Hoover Institution and president of Shalem College in Jerusalem. One of pioneers of podcasting, he's been hosting EconTalk since 2006.🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @EconTalkerEconTalk Website: www.econtalk.orgEconTalk YouTube Channel⌛TIMESTAMPS(03:25) - The influence of Russ' father
(11:13) - What modern economics often fails to observe
(16:15) - Adam Smith and human nature
(27:05) - Starting EconTalk in 2006
(40:42) - Moving to Israel in his 60's
(45:35) - How people misunderstand the Academia
(49:43) - How Russ' approach to his podcast developed over time
(53:01) - The metaphor of a conversation
(57:11) - Mortality & fatherhood
(01:03:49) - Russ' dream guest and what's next
📕Buy Paul’s Book: The Pathless Path🤝Join Find The Others: A Community For People On Unconventional Paths📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here
Mar 6, 2023 • 1h 11min
#136 Complexity & Complicatedness - Sam Spurlin on playing hockey, why he quit teaching, studying at Claremont, leaving a PhD program, working pro bono too start his career, complicated vs complex systems, how to deal with ego in organizations, remote work failures, podcasting with his brother, and the importance of a retrospective meeting
Sam is a partner at The Ready - an organizational design consultancy operating fully remotely. He is also a prolific writer, passionate about personal development, self-managing organizations and adopting a more human, adaptive, and meaningful way of working.🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @samspurlinInstagram: samspurlinLinkedIn: linkedin.com/in/samspurlinSam's writing: samspurlin.com/writingSam's writing on Medium: samspurlin.medium.comNewsletter: thedeliberate.substack.com/p/landing-page⌛TIMESTAMPS(00:53) - The scripts that Sam grew up with
(10:09) - Teaching and why Sam quit
(17:10) - Claremont and letting go of the PhD
(25:49) - Working pro bono to become a consultant
(31:26) - Complicated vs complex systems, ego in the organizations
(53:49) - Writing, podcasting, farming and retrospective meetings
(01:02:02) - The trap of a "dream job"
(01:05:27) - Closing remarks
📕Buy Paul’s Book (Published Jan 2022): The Pathless Path😁👉😁 Want To Connect, Create & Root For Others On The Pathless Path? - Join 100+ Others In The Find The Others Community📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here
56 snips
Feb 27, 2023 • 1h 9min
#135 Beyond Comfort - Derek Sivers on why great musicians shake things up, ambition, and moving to a new country as a superpower, lessons from Singapore, and the scripts around having children
Derek Sivers has been a musician, producer, circus performer, successful entrepreneur, TED speaker, and book publisher. He has lived all around the world and has never let himself be too comfortable - constantly changing and following his inner ambition.🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @siversWebsite: sive.rsMy Favorite Derek Book: Anything You Want⌛TIMESTAMPS(00:54) - The scripts that Derek grew up with
(05:45) - Comfort as a plateau that needs to be shattered
(11:46) - Travel as a tool to change your life
(17:26) - Beliefs and actions
(22:48) - Learning from other people's approaches to life
(27:44) - Derek's future and how to learn from when our lives go off track
(33:53) - Scripts around having kids
(45:03) - Retirement & Ambition
(56:25) - Closing remarks
📕Buy Paul’s Book (Published Jan 2022): The Pathless Path😁👉😁 Want To Connect, Create & Root For Others On The Pathless Path? - Join 100+ Others In The Find The Others Community📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here
6 snips
Feb 20, 2023 • 1h 27min
#134 The Office-Based Reality is Over - Dror Poleg on entrepreneurship in Israel, studying in Australia, working in China, Future of Remote Work and The Real Estate Business, How To Write A Top 5 Book in Almost Any Category, The Disappearance of The Middle-Skilled Job, Inequality and The End of The Offices
Dror worked as a real estate private equity exec, startup founder, front-end developer, parliamentary advisor, and soldier. Having lived all around the world he is now based in NYC, writing as an “Economic Historian”.Having predicted that remote work is going to become the new norm back in 2015, he has just published a survival guide titled "After Office".🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @drorpolegWebsite: drorpoleg.comAfter Office ⌛TIMESTAMPS (13:30) - Living in Australia and China
(23:10) - Writing and Work in Dror's life
(27:46) - Remote Work and Real Estate
(42:26) - Using information from the Internet - writing a top 5 book
(49:42) - Unconventional Paths and The Disappearance of The Middle-Skilled Jobs
(58:56) - Inequality, Luck, and Challenges for The US
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here
19 snips
Feb 13, 2023 • 1h 8min
#133 Creation Without The Ego - Isabel Unraveled on writing, "the chronic state of performing", detaching your sense of self from the work, finding the inner child, paying attention to your emotions, trusting your intuition and why people should stop pretending
Isabel is a writer who is very passionate about the creative process. She has some powerful original ideas about the relationship between the artist and their creation, trusting one's intuition, and why people should stop pretending.🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @isabelunraveledIsabel's Writing: https://mindmine.substack.com⌛TIMESTAMPS(0:11) Introduction (5:41) "The chronic state of performing" (12:00) Missing and rediscovering her passion for writing (34:38) Detaching your sense of self from the work (41:52) The inner child (53:02) Why people should just stop pretending? (1:00:30) How Isabel thinks (or doesn't think) about her future? (1:04:09) Closing remarks 📕Buy Paul’s Book (Published Jan 2022): The Pathless Path 😁👉😁 Want To Connect, Create & Root For Others On The Pathless Path? - Join 100+ Others In The Find The Others Community📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here
26 snips
Feb 6, 2023 • 1h 11min
#132 Making Money Simple & Smart - Nick Maggiulli on blogging into a new career, writing for smart people, building relationships in the finance world, the lifestyle creep myth, dying with too much money, and money emotions
Nick Maggiulli is a finance data analyst and writer. He is the author of "Just Keep Buying" and has a blog titled "Of Dollars and Data".🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @dollarsanddataBlog: Of Dollars and DataNick's Book: Just Keep Buying ⌛TIMESTAMPS(0:47) The scripts nick grew up with(5:35) Writing books and blogging(32:44) Building relationships in the NYC finance scene(36:07) Why the writers shouldn't dumb down their books(37:33) Perceptions of money(1:07:26) Closing thoughts📕Buy Paul’s Book: The Pathless Path🤝Join Find The Others: A Community For People On Unconventional Paths📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here
37 snips
Jan 30, 2023 • 1h 29min
#131 The Art of Sabbaticals - Cécile and Michelle on finding "forgotten hobbies", writing online, improving their relationship with money, abundance mindset and rediscovering joy
Cécile has had a successful career in consulting, acquiring a senior position in a big company that has taken a leadership role in the energy transition in the UK. Although she was passionate about her job she decided to go on a yearlong sabbatical from work, traveling around the world and writing - creating space for her curiosity & creativity.Michelle has a background in sales but after a couple of years in the business she decided to go on a sabbatical that doesn't seem to have an end. When she isn't busy fending off people who constantly try to hire her, she runs a podcast with her sister - "Status Post Adulting Podcast" and she has written multiple essays, while slowly "getting famous for not working" in the meantime.🎥🍿 YOUTUBE: WATCH HERECécile:Twitter: @cecile_mcmWebsite: https://www.cecilemarion.org/Book a 1-on-1 Call With Cecile (Gift Economy): Book HereMichelle:Twitter: @mvarghooseMichelle's Essays: NewsletterPodcast: Status Post-AdultingMy Essay On The Ultimate Guide To Sabbaticals⌛TIMESTAMPS(0:00) Audio intro(2:27) Deciding to go on a sabbatical (25:29) "There is nothing to do" - rediscovering joy (30:05) Lowering the cost of living (46:58) How people change on a sabbatical - discovering writing (1:08:30) Getting famous for not working, the gig economy(1:11:17) The role of writing in Cécile's journey (1:15:37) Returning to work - closing thoughts📕Buy Paul’s Book (Published Jan 2022): The Pathless Path 😁👉😁 Want To Connect, Create & Root For Others On The Pathless Path - Join 75+ Others In The Find The Others Community📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial
📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here
